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Ashland Condominium Resorts to Rent

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Ashland condo resorts

A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (864 reviews)
"Clean, comfortable, spacious rooms with good service. Nice place to stay while in the area."
United States
Jerrold
$149 nightly
The price is $161
Sep 8 - Sep 9
Total with taxes and fees
Hotel Vienna
A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

2. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (149 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
$139 nightly
The price is $150
Oct 1 - Oct 2
Total with taxes and fees
Cave Mountain Motel
A swimming pool with lounge chairs and potted plants.

3. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.8 out of 10, Excellent, (176 reviews)
"Great accommodations for the price. The room was quiet and comfortable. Great value, and I'll definitely be staying here again."
United States
Cory
$120 nightly
The price is $130
Sep 7 - Sep 8
Total with taxes and fees
Moore's Motel
A covered porch with outdoor seating, a staircase, and potted plants.

4. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (488 reviews)
"Great place to stay!"
United States
Eric
$81 nightly
The price is $89
Oct 6 - Oct 7
Total with taxes and fees
The Colonial Motel
A river flowing through a forested area with rocks and autumn-colored trees.

5. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (153 reviews)
"Perfect quiet little motel close to great hikes. Staff was courteous and had tons of information on things to do in the area."
United States
Gerald
$149 nightly
The price is $161
Sep 7 - Sep 8
Total with taxes and fees
Black Bear Lodge
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

6. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,012 reviews)
"great hotel"
United States
Yaacov
$140 nightly
The price is $152
Sep 22 - Sep 23
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

7. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (363 reviews)
"Great place for a couple."
United States
Abdul
$167 nightly
The price is $180
Sep 7 - Sep 8
Total with taxes and fees
The Winwood Condominiums
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

8. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (137 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Sep 8 - Sep 9
Total with taxes and fees
Antique Rose Inn Windham
A large, two-story house with multiple porches and string lights.

9. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (286 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Sep 7 - Sep 8
Total with taxes and fees
Albergo Allegria Hotel
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

10. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
8.6 out of 10, Excellent, (4 reviews)
"What a gem of a property! The brother and sister that own and operate this place are so sweet and hospitable, and the bar and motel are quaint and charming in a cozy, woodsy way. If I’m ever in the area I would absolutely stay here again."
United States
Amy
$135 nightly
The price is $146
Oct 6 - Oct 7
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
A bedroom with a large window, a bed, and a view of a forest.

11. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (34 reviews)
"Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up...
United States
Raven Jane
$260 nightly
The price is $281
Sep 30 - Oct 1
Total with taxes and fees
The Haüs Windham
A park with Adirondack chairs and a table, surrounded by trees.

12. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (302 reviews)
"Service and breakfast were very good"
United States
Daniel
$169 nightly
The price is $183
Sep 10 - Sep 11
Total with taxes and fees
Mountain Treasure B&B
A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

13. SunView Motel

SunView Motel
2.5 star property
Tannersville
8.6 out of 10, Excellent, (608 reviews)
"Great hotel!"
United States
Victoria
$118 nightly
The price is $128
Oct 1 - Oct 2
Total with taxes and fees
SunView Motel

14. The Wheelhouse Inn

The Wheelhouse Inn
2.5 star property
Pine Hill
8.6 out of 10, Excellent, (131 reviews)
"The location is convenient for Belleyare skiers."
United States
Allen
$90 nightly
The price is $101
Sep 11 - Sep 12
Total with taxes and fees
The Wheelhouse Inn
A room with a view of a landscape through a window, a chair, a table with a laptop, and a bed with books on it.

15. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (40 reviews)
"Really well kept friendly staff and was overall a joy to stay at The Perch! No complaints what so ever."
United States
Jason
$208 nightly
The price is $225
Sep 10 - Sep 11
Total with taxes and fees
The Perch Hotel
A multi-story building with outdoor seating and a stone-paved patio.

16. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (419 reviews)
"Great location to amazing trails and great accommodations"
United States
Nuria
$208 nightly
The price is $225
Sep 21 - Sep 22
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

17. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (116 reviews)
"The staff was friendly and the room was clean and comfortable. Would love to come back again!"
United States
Claire
$272 nightly
The price is $293
Sep 14 - Sep 15
Total with taxes and fees
Eastwind Windham
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

18. Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
Tannersville
9.8 out of 10, Exceptional, (595 reviews)
"very nice location and staff"
United States
Qiang
$175 nightly
The price is $189
Sep 7 - Sep 8
Total with taxes and fees
Hotel Mountain Brook
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

19. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (124 reviews)
"Wonderful stay"
United States
Yousung
$347 nightly
The price is $374
Sep 24 - Sep 25
Total with taxes and fees
Wylder Hotel Windham
A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

20. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (286 reviews)
"Host was very nice and bed was clean and comfortable. The bathroom in our room was newly renovated and the big shower had great water pressure!"
United States
Margo
$132 nightly
The price is $145
Sep 13 - Sep 14
Total with taxes and fees
Shadowcrest
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

8/10 Good
"Clean , comfortable , did not use amenities bc we arrived too late . They had an indoors pool , a couple of places where you could make and sit by the fire and a corn hall . Breakfast was ok . Cereals, variety of coffees or tea . Various croissants and yougurt !"
Roxana 1-night trip
Posted 5 hours ago
Hotel Vienna

Find out more about Ashland

Ashland Condo Resorts information

Number of reviews
5,221
Accommodation
0 Condo Resorts
Lowest Price
$89
Highest Price
$374

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